The package arrived in the mail looking like a communiqué from a spy agency: an outer envelope with only my name and address and the cryptic “Guess Where Trips’ logo in the corner. Inside, a dossier containing 5 sealed envelopes, and a printed ‘Hey Travellers!’ introductory note, telling me that I must open the envelopes in the order specified, starting with the one titled Before You Go. I was hooked! In my hands I held everything that Henk and I needed to set out on a surprise day trip from Toronto that promised to deliver ‘”outdoor adventures and scenic roads”, and all we needed to do was start by opening the first envelope. Curious, impatient and eager to know what was in store for our day, I ripped into the first envelope and our adventure began!

Guess Where Trips: Sponteneity Wrapped Up in Detailed Planning

The concept behind Guess Where Trips is fun and simple: instead of you doing all the planning for your road trip, researching where to go and what to do when you get there, someone else does the work for you, curating interesting experiences and stops along the way. The company offers all kinds of surprise day trips from Toronto, as well as from other major cities in Ontario and Canada. All you have to do is pick the theme for your trip based on a few parameters (your origin city, how far you want to drive), and a few preferences (family-friendly, food-centric, outdoorsy, etc) and then you are served up a themed package with all the details you’ll need for a ready-made day trip.

As a super-planner when it comes to all of our own day trips from Toronto and elsewhere, I have to admit it was very liberating to give up control and leave behind all the legwork – and guesswork. And since a surprise road trip sounded like just the sort of adventure our Covid-weary routine needed, Henk and I excitedly piled into the car and set off.

Our Day Trip from Toronto: SPOILER ALERT!

If you don’t want to know where our Guess Where Trips package took us and what Henk and I saw and did, stop reading now! But if you would like to see where our road trip adventure led, read on – because this turned out to be one of the best day trips from Toronto that we’ve taken!

Envelope 1: “Before You Go”

Our first envelope was a practical one, offering up tips for what we should wear, how long we could expect to be on the road, distance between stops, how much time to allot at each stop, etc. It was actually recommended that we open this envelope in advance of our actual trip, so we would have some information to help us choose our departure day, while still keeping the destination a mystery.

Our next Envelope: Our First Stop

It was a particularly beautiful Sunday morning in September when Henk and I decided to pull the trigger on our Toronto day trip. Like two kids excited to open a present, we unsealed the first envelope, where we learned that we would be going east from Toronto, en route to Port Hope, “a cute town with a few surprises'” about 2 hours away. So we donned our sunglasses, piled into the car and hit the road!

TIP: The Guess Where Trips envelope even included a QR code that brought up our destination on our cell phone to help with directions.

One of the surprises mentioned in our itinerary turned out to be a “ghost town” along the way called Wesleyville that was listed as an optional pit stop. Always game to see a ghost town, (provided there are no actual ghosts), Henk and I took this short detour to explore what was left of this 19th-century hamlet. All that remains today of this former town is a schoolhouse built in 1860, and a church dating from 1899, both of which are being restored by the local community. But what was more interesting to Henk and I was the church graveyard, as it holds families that date back generations.

Walking around this cemetery we did find a few particularly photogenic gravestones – some cryptic (pardon the pun!), some succinct, and some with a sense of humour.

TIP: Even though visitors are welcome, always try to be respectful when visiting any type of cemetery, whether it is a rural one in wine country tied to a bit of local lore, or a famous one in Argentina with infamous names on the tombs.

“A Town with a Story”: One of Ontario’s Best Preserved Main Streets

Next up on our road trip was Port Hope, a charming town of about 16,000 people that neither Henk nor I had ever visited. The town definitely lived up to its reputation as ‘cute’, but not just because of its large number of heritage buildings in the historic downtown (which makes this particular downtown one of the largest and best preserved in Ontario).

Port Hope also has cute boutiques on Walton, it’s main street, featuring local designer clothing (check out Poho Boho), funky and on-trend home decor stores, and of course several nice cafes and restaurants. Plus there were beautiful walking paths along both sides of the Ganaraska River that flows through the downtown.

But the surprise even the Guess Where Trips organizers couldn’t have planned waited for us in the actual Ganaraska River itself: dozens of people standing shin-deep in the water along the edges of the river, fishing rods and nets in hand.

It turns out that by pure coincidence, Henk and I had timed our visit at the end of the Ganaraska River salmon run!

A Serendipitous Salmon Run

The first time Henk and I had seen a salmon fun was on Manitoulin Island at Bridal Veil Falls, so once we realized what was happening, we parked ourselves on the pedestrian bridge that spans the river for a bird’s eye view of the action.

Dozens of enormous salmon were swimming upstream below us, the occasional one taking the bait of a lucky fisherman who then had to negotiate the current, avoid getting tangled in other fishing lines, and try to land the struggling fish.

Kudos to the successful fishermen and fisherwomen who managed to reel in one of these 20-plus-pounders, and what a treat to be able to watch it all go down from our sunny perch.

Our surprise salmon run kept us in Port Hope longer than expected, but that is the beauty of a mystery road trip: you never know what you’ll find. All the same, I was keen to head to another place featured on our itinerary that I had actually discovered myself months ago when I was researching day trips in Ontario, but never had a chance to visit: a larger-than-life store-cum-attraction called Primitive Designs.

Primitive Designs Appeals to the Kid in Everyone

When I first found Primitive Designs online, I couldn’t wait to take a trip out to see this place for myself. So I was thrilled when I saw that our Guess Where Trips itinerary included this stop just outside of Port Hope. What I wasn’t prepared for was the popularity of this place, probably more so on the day we arrived because it happened to be a gorgeous sunny Sunday.

One look at the 26-foot tall Transformer welcoming visitors at the entrance and it was easy to see why this place attracts all kinds of people, from families with kids, to gamers, to shoppers who love the exotic, to forever-young grownups like Henk and I. After all, who wouldn’t want to see Optimus Prime ‘in the flesh’, or life-sized dinosaurs and velociraptors made out of recycled metal salvage, not to mention mythical creatures, and oh, yes, an Iron Throne! But just exactly what was this place and what was the story behind it?

So Much More Than a Retail Store

Despite appearances to the contrary, Primitive Designs is not some kind of amusement park; the barn-sized central building is actually a massive retail shop that houses all kinds of exotic imported goods and artesanal products from around the world. There are colourful chimineas, beautiful wood carvings, mosaic bowls, textiles and masks.

But without a doubt it is the larger-than-life sculptures and art pieces around the property that have put Primitive Designs on the map.

I was curious to know how all this had come about, so when I spotted someone who looked like he was in charge, I went up to him and introduced myself. My instincts were correct, as the man in charge was Ron Dacey, who is not just the owner of Primitive Designs along with his wife Rhonda and son Maximus, but the creative mind behind the giant installations here.

A self-proclaimed hippy who lived the couch-surfing, back-packing life of a free spirit in his youth, Ron is a born entrepreneur. Even while travelling the world on a shoestring, he saw opportunity in every craft market he visited, buying the unique products he found and selling them to Europeans to help fund his travels.

Ron’s humble start selling products from the back of his Volkswagen evolved into a successful business as an importer in Toronto. He translated his passion for travel and his eye for exotica into a 17-year business as a vendor at Toronto’s Harbourfront Antique Market. It was in Toronto where Ron met Rhonda Cook, a businesswoman herself who had worked in the eclectic Queen Street West neighbourhood for years. But it was when the two of them decided to move to Port Hope and establish Primitive Designs twenty years ago or so, that Ron got to really indulge his creative side – in a big way.

A Global Enterprise

Working with overseas artisans he has met during his global travels and buying trips, Ron translates his own creative sketches and designs into giant handcrafted art pieces. Built in southeast Asia using upcycled metal salvage, these giant sculptures are shipped to the Port Hope property where they are assembled and installed by Ron and his team.

In pre-Covid years, Ron would typically swing by these overseas workshops during his travels to check on the progress of said sculptures, but for the past two years because of Covid, he’s been relying on long-distance communication only. But that has also given him time to get more hands-on with some of the builds, like the Kraken attacking a sailing ship, where Ron did much of the re-design and construction of the ship himself.

A Family Affair

Primitive Designs is definitely a passion project for the whole family: Rhonda manages much of the retail business, and it was their son Max who did all the research on the dinosaurs to ensure that the metal versions you see on the property are actually built to scale, with details based on actual dinosaur specimens that have been discovered and documented.

And when they aren’t working their Primitive Design business, you’ll find Ron and Rhonda down in Belize where they have a few other projects on the go. (And yes, I’m a little jealous of their lifestyle, I gotta say!)

TIP: It’s free to visit Primitive Designs and photograph any of their art pieces, but there are ‘donation buckets’ beside them if you’d like to contribute to help support Ron and Rhonda’s charity work in Belize.

Our Second Stop… “An Easy Adventure”, but first…Goats!

The beautiful thing about surprise adventures is you never know who you will meet or where you might end up, which in our case turned out to include a short detour from our planned itinerary to check out a business that Rhonda had recommended…the Haute Goat farm a short drive from Primitive Designs.

Haute Goat Farm

Like the name suggests, Haute Goat Farm is very goat-centric, from goat yoga classes that are offered al fresco in the warmer months, to the Screaming Goat cafe on-site that serves locally-sourced goat milk products like ice cream and a particularly delicious mac ‘n’ goat cheese. But the farm is also a great destination for a rural outing with lots of trails available on the farm and the opportunity to interact with other animals, including Alpacas.

Kids would love this farm experience, but there are also activities that cater more to grownups, including an overnight B&B package called the Alpaca Sleepover where you can stay in a comfy cabin inside the Alpaca enclosure, and wake up to the sound of roosters.

Our impromptu visit meant that Henk and I only had time for a short visit, but the unexpected detour made for a nice stop for lunch and was worth checking out since we were literally in the neighbourhood.

TIP: If you don’t want to sleep overnight next to the Alpacas, visitors can book an ‘Alpaca Knuffle Shuffle” where you can get to engage with Alpacas and walk them along some of the trails.

Speaking of farms and trails….

After briefly saying hello and goodbye to the goats and alpacas, Henk and I got back onto our Guess Where Trips itinerary, and headed out for a hike in the Carstairs Tract, the ‘easy adventure’ promised in our Second Stop.

Seventy-five years ago Carstairs Tract was cleared for farming, but the property has since been replanted first as an educational arboretum, and later with more local tree species. Today this accessible forest offers pretty shaded trails where visitors can learn how to identify local trees, or just enjoy an easy shaded walk. (which in our case involved photographing some interesting mushrooms, too.)

Our Third Stop: “An Italian Countryside”

Wait, what? There’s an Italian vineyard in Northumberland County?

Welcome to Villa Conti, 100 acres of rolling hills owned by Italian chef Tommaso Conti, who had his eye on this rural property for several years before purchasing it and moving here in 2015. An experienced restauranteur and caterer who owned a restaurant in Toronto for many years, Conti’s dream for the Villa was to open a restaurant offering authentic rustic Italian dishes, restore the neglected vineyards in order to produce his own wine, and recreate a bit of his own rural Italian upbringing.

Again, as luck would have it, our timing was perfect for our visit: Henk and I happened to arrive on the same day that Tommaso was hosting a thank-you lunch for friends and family who has just helped bring in the grape harvest. Lunch was over but it looked like the celebration was just starting, because before we knew it, kids and adults alike were crushing grapes alla ‘Lucille Ball’, up to their knees in purple grape juice and stomping their bare feet to the tune of La Tarantella.

Tommaso invited Henk and I to join in, but even though we didn’t stomp the grapes ourselves, we definitely felt like we were part of the festivities. With the late afternoon sun turning the vineyards golden, a plate of charcuterie to share and a glass of ‘Villa Conti Red’ in hand, we could just as easily have been somewhere in the Abruzzese countryside! Salute!

Our Fourth Stop. “Choose Your Own Adventure”…or Save it ’til Later…?

The best thing about a Guess Where Trip is that you open each envelope one at a time, keeping the mystery alive until the next destination and its attractions are revealed. However, when you are like Henk and I, and take the time to ‘do it all’ at each stop, it’s easy to run out of time in your day before completing all 4 stops. Which is exactly what happened. Before we could begin to do justice to the places listed in our fourth envelope, the sun had dipped pretty low on the horizon, and we knew we wouldn’t have time to take advantage of all the things still left to see and do on this particular day trip from Toronto.

Which means only one thing: there’s another road trip in our future!!!!

That’s the great thing about one of these road trips….we can choose to ‘complete’ it whenever we want to, and having peeked at the suggestions in that last envelope, there’s easily enough for a full day’s worth of hiking, photography, dining and even beer! Plus there are other food stops en route to sample buttertarts and other goodies that we didn’t have time for on this trip.

Removing the Guesswork with Guess Where Trips

If you are even half as curious as Henk and I, love a little mystery, and like to take advantage of the serendipitous surprises that might appear along the way, a Guess Where Trip could be just your thing. Our Sunday drive turned out to be one of our best day trips from Toronto ever, and thanks to someone else doing all the planning, the guesswork was taken out of the whole process for us.

One thing still remains a mystery, though, and that is: what unexpected and interesting things are left to discover in that fourth envelope? Are you as curious as Henk and I to see what awaits…?

I guess you’ll just have to wait to find out, too!

TIP: Guess Where Trips packages cost $55 before tax and shipping. As a nice bonus, the organizers have negotiated special offers and discounts at many of the businesses they list, so look for these discounts in your itinerary and mention them if you do visit those places. And if you want to make your day trip into an overnight trip, just contact the Guess Where Trips folks who will be happy to make some suggestions for where to stay. How easy is that?